Isovaleryl chloride → 6-Chloro-2-(4-chloropyridine-2-carbonyl)-3-(isovalerylamino)indole

HRID 379866Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=1)=[O:13].[C:21](Cl)(=[O:26])[CH2:22][CH:23]([CH3:25])[CH3:24]>>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([NH:1][C:21](=[O:26])[CH2:22][CH:23]([CH3:25])[CH3:24])=[C:3]([C:12]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=3)=[O:13])[NH:4]2)=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 66054Isovaleryl chloride

HCID 183681263-Amino-6-chloro-2-(4-chloropyridine-2-carbonyl)indole

Product 1

HCID 183681076-Chloro-2-(4-chloropyridine-2-carbonyl)-3-(isovalerylamino)indole

Procedure

The title compound was prepared according to the procedure described in Example 19 from 3-amino-6-chloro-2-(4-chloropyridine-2-carbonyl)indole (Example 68) and isovaleryl chloride. m.p.: 183-184° C. (recrystallized from ethyl acetate) 1H-NMR (DMSO-d6) δ: 11.67 (1 H, br s), 10.08 (1 H, br s), 8.69 (1 H, d, J=5.3 Hz), 8.52 (1 H, d, J=9.2 Hz), 8.37 (1 H, d, J=2.1 Hz), 7.57 (1 H, dd, J=2.0, 5.3 Hz), 7.39 (1 H, d, J=2.0 Hz), 7.06 (1 H, dd, J=2.0, 9.6 Hz), 2.46-2.30 (3 H, m), 1.09 (6 H, d, J=6.4 Hz).

Workup

customm.p.: 183-184° C. (recrystallized from ethyl acetate) 1H-NMR (DMSO-d6) δ: 11.67 (1 H, br s), 10.08 (1 H, br s), 8.69 (1 H, d, J=5.3 Hz), 8.52 (1 H, d, J=9.2 Hz), 8.37 (1 H, d, J=2.1 Hz), 7.57 (1 H, dd, J=2.0, 5.3 Hz), 7.39 (1 H, d, J=2.0 Hz), 7.06 (1 H, dd, J=2.0, 9.6 Hz), 2.46-2.30 (3 H, m), 1.09 (6 H, d, J=6.4 Hz)

Sources & evidence

ORD record: ord-3bd73a71f9b8407f826f87d99cffc0e8
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300363B1

Reaction notes

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